Should I Convert House Hack to Airbnb?

[Ben Cohen]

Hi everyone,

I'm closing on my first owner-occupied SFH at the end of this month. It's a 3/2 in the desirable Wilton Manors (Broward County, Florida) that I'll be paying out of pocket around 500-600 a month to live in once I get roommates.

Thinking ahead, once I eventually move on to the next property, I'm considering Short Term Rentals. The Airbnb/VRBO nightly rates in this area are insane ($300-400/night for the nice 3/2s) but 100% of them have a pool, and the house I'm closing on does not. 

Here are some options I've considered:

1. $70k total: Build an in-ground pool for 50-60k, add a nice deck & outdoor tiki area etc. With financing I could have a monthly payment of 300 or so for the pool which isn't so bad - but this is for a term of 20 years. (Is pool financing smart or foolish if it's for a STR investment property?)

2. $20k total: Install an above-ground pool that is partially dug into the ground, build a deck around it. See pictures here for reference: https://www.instagram.com/p/CC.... The property will have a pool, but I fear it'll always be less attractive than an in-ground pool to the point that I'd have high vacancy or be forced to lower my nightly rate.

3. $20k total: Build out the backyard with a jacuzzi/bar/tiki area.

4. $0 additional: Continue living here as a house hack and invest my money in other real-estate ventures, whether Airbnb or long-term rental.

Thank you all for your insight!